On the eve of a big Valentine's Day party being given by Capeside High's resident hedonist, Matt Caulfield, Joey reluctantly agrees to attend, if only to keep Dawson out of trouble. As Andie and her friends prepare for the party too, Jack's old girlfriend, Kate Douglas, arrives in town having just discovered that her current boyfriend is gay. And as Jack hesitates to reveal that he's also gay, Pacey encourages Dawson to try and catch Kate on the rebound. Meanwhile, Henry sells his own blood to raise the money for a first date with Jen.

In the wake of Matt Caufield's expulsion, Principal Green comes under fire from an angry Capeside community. Under considerable pressure himself, Superintendent Byron Fielding makes it clear that if he doesn't rescind the expulsion order, Green will be asked to resign. Pressed to rally some support for their embattled principal, Joey calls on A.J. for guidance, especially after seeing television journalist Sherry Eisler's one-sided report. And after Dawson offers to help revive her journalistic career, Gail tries to set the record straight with a balanced report on Green's plight.

In preparation for their ritual Spring Break visit with his Aunt Gwen, Dawson and Joey invite Andie and Jack to join them. When Jack begs off at the last minute, Pacey asks if he and an old friend who's back in Capeside for a visit can come along, too. And while Pacey and Joey do their best to avoid any uncomfortable confrontations, Andie takes a liking to the enigmatic Will Crudski. Back at the restaurant, Mitch and Gail learn about the untimely death of an old friend who was the best man at their wedding, while Jen discovers that one of the waitresses is interested in Henry.